N-bromobutanimide → Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate

HRID 1476074ノート

反応式

HRID 1476074 の反応式
[F:1][C:2]([F:19])([F:18])[CH:3]([CH3:17])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:20]N1C(=O)CCC1=O>ClC(Cl)Cl>[Br:20][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH:4]([CH:3]([CH3:17])[C:2]([F:18])([F:19])[F:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:14]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 58136599Ethyl 4,4,4-trifluoro-3-methyl-2-(4-methylphenyl)butanoate

生成物 1

HCID 58136537Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

2.25 g (8.2 mmol) of ethyl 4,4,4-trifluoro-3-methyl-2-(4-methylphenyl)butanoate, 1.53 g (8.6 mmol) of N-bromosuccinimide and 67 mg (0.41 mmol) of 2,2′-azobis-2-methylpropanenitrile in 36 ml of trichloromethane were stirred under reflux overnight. After the reaction had gone to completion, the succinimide was filtered off, the filter residue was washed with dichloromethane and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 40:1). This gave 2.667 g (7.5 mmol, 92% of theory) of a yellowish oil.

後処理

  1. temperatureunder reflux overnight
  2. filtrationthe succinimide was filtered off
  3. washthe filter residue was washed with dichloromethane
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 40:1)

出典と根拠

ORDレコード
ord-95a38640228e4c74beaf4db7eb7b4e56
出典データセット
uspto-grants-2015_04
特許番号
US09018414B2

反応ノート

読み込み中…